Chemistry for Today: General  Organic  and Biochemistry
Chemistry for Today: General Organic and Biochemistry
9th Edition
ISBN: 9781337514576
Author: Seager
Publisher: Cengage
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Textbook Question
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Chapter 14, Problem 14.11E

Each of the following names is wrong. Give the structure and correct name of

each compound.

a 3-ethyl-2-butanone

b 2-ethyl-propanal

c. 4-methyl-5-propyl-3-hexanone

d. 2-methyl-2-phenylethanal

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation:

The structural formula of 3-ethyl-2-butanone is to be drawn and its correct name is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

Rules for writing the structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ane, ene, yne, ol, al and so on.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Aldehydes and ketones contain carbonyl Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  1 functional group in their parent chain and are named by adding suffix –al and –one to the name of the parent alkane.

Answer to Problem 14.11E

The structural formula of 3-ethyl-2-butanone is,

Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  2

The correct name is 3-methyl-2-pentanone.

Explanation of Solution

The given name is 3-ethyl-2-butanone. The root word used in this is ‘but’. It means structure contains four carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One ethyl substituent is attached to the third carbon atom. The functional group present in the given compound is ketone (R-CO-R) because the suffix used for ketone is –one. It is present at the second carbon atom. Therefore, the structure corresponding to 3-ethyl-2-butanone is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  3

Figure 1

The longest carbon chain contains five carbon atoms. One methyl substituent is attached to the third carbon atom. The functional group present in the given compound is ketone (R-CO-R) present at the second carbon atom. Therefore, the correct name of this compound is 3-methyl-2-pentanone.

Conclusion

The structural formula is shown in Figure 1.

The correct name of the compound is 3-methyl-2-pentanone.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation:

The structural formula of 2-ethyl-propanal is to be drawn and its correct name is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

Rules for writing the structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ane, ene, yne, ol, al and so on.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Aldehydes and ketones contain carbonyl Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  4 functional group in their parent chain and are named by adding suffix –al and –one to the name of the parent alkane.

Answer to Problem 14.11E

The structural formula of 2-ethyl-propanal is,

Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  5

The correct name is 2-methylbutanal.

Explanation of Solution

The given name is 2-ethyl-propanal. The root word used in this is prop. It means structure contains three carbon atoms. One ethyl substituent is attached to the second carbon atom. The functional group present in the given compound is aldehyde (R-COH) because the suffix used for aldehyde is –al. It is present at the first carbon atom. Therefore, the structure corresponding to 2-ethyl-propanal is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  6

Figure 2

The longest carbon chain contains four carbon atoms. One methyl substituent is attached to the second carbon atom. The functional group present in the given compound is aldehyde (R-COH) present at the first carbon atom. Therefore, the correct name of this compound is 2-methylbutanal.

Conclusion

The structural formula is shown in Figure 2.

The correct name of the compound is 2-methylbutanal.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation:

The structural formula of 4-methyl-5-propyl-3-hexanone is to be drawn and its correct name is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

Rules for writing the structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ane, ene, yne, ol, al and so on.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Aldehydes and ketones contain carbonyl Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  7 functional group in their parent chain and are named by adding suffix –al and –one to the name of the parent alkane.

Answer to Problem 14.11E

The structural formula of 4-methyl-5-propyl-3-hexanone is,

Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  8

The correct name is 4, 5-dimethyl-3-octanone.

Explanation of Solution

The given name is 4-methyl-5-propyl-3-hexanone. The root word used in this is hex. It means structure contains six carbon atoms. One methyl substituent is attached to the fourth carbon atom and one propyl group is attached to the fifth carbon atom. The functional group present in the given compound is ketone (R-CO-R) because the suffix used for ketone is –one. It is present at the third carbon atom. Therefore, the structure corresponding to 4-methyl-5-propyl-3-hexanone is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  9

Figure 3

The longest carbon chain contains eight carbon atoms. One methyl substituent is attached to the fourth carbon atom and the other methyl group is attached to the fifth carbon atom. The functional group present in the given compound is ketone (R-CO-R) present at the third carbon atom. Therefore, the correct name of this compound is 4, 5-dimethyl-3-octanone.

Conclusion

The structural formula is shown in Figure 3.

The correct name of the compound is 4, 5-dimethyl-3-octanone.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation:

The structural formula of 2-methyl-2-phenylethanal is to be drawn and its correct name is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

Rules for writing the structural formula from IUPAC are:

• First identify the word root for the given compound.

• The suffix used in the compound like –ane, ene, yne, ol, al and so on.

• Identify the position, location, and number of the substituent bonded to the carbon chain.

Aldehydes and ketones contain carbonyl Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  10 functional group in their parent chain and are named by adding suffix –al and –one to the name of the parent alkane.

Answer to Problem 14.11E

The structural formula of 2-methyl-2-phenylethanal is,

Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  11

The correct name is 2-phenylpropanal.

Explanation of Solution

The given name is 2-methyl-2-phenylethanal. The root word used in this is eth. It means structure contains two carbon atoms. One methyl and one phenyl substituents are attached to the second carbon atom. The functional group present in the given compound is aldehyde (R-COH) because the suffix used for aldehyde is –al. It is present at the first carbon atom. Therefore, the structure corresponding to 2-methyl-2-phenylethanal is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 14, Problem 14.11E , additional homework tip  12

Figure 4

The longest carbon chain contains three carbon atoms. One phenyl substituent is attached to the second carbon atom. The functional group present in the given compound is aldehyde (R-COH) present at the first carbon atom. Therefore, the correct name of this compound is 2-phenylpropanal.

Conclusion

The structural formula is shown in Figure 4.

The correct name of the compound is 2-phenylpropanal.

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Chapter 14 Solutions

Chemistry for Today: General Organic and Biochemistry

Ch. 14 - Each of the following names is wrong. Give the...Ch. 14 - Each of the following names is wrong. Give the...Ch. 14 - Prob. 14.13ECh. 14 - Prob. 14.14ECh. 14 - Prob. 14.15ECh. 14 - Explain why propane boils at 42C, whereas ethanal,...Ch. 14 - Use a dotted line to show hydrogen bonding between...Ch. 14 - Use a dotted line to show hydrogen bonding between...Ch. 14 - Prob. 14.19ECh. 14 - Prob. 14.20ECh. 14 - Prob. 14.21ECh. 14 - Prob. 14.22ECh. 14 - Prob. 14.23ECh. 14 - Prob. 14.24ECh. 14 - Label each of the following as acetals, ketals, or...Ch. 14 - Label each of the following as acetals, ketals, or...Ch. 14 - Label each of the following structures as a cyclic...Ch. 14 - Label each of the following structures as a...Ch. 14 - What two functional groups react to form the...Ch. 14 - Hemiacetals are sometimes referred to as potential...Ch. 14 - Complete the following statements: a. Oxidation of...Ch. 14 - Prob. 14.32ECh. 14 - Prob. 14.33ECh. 14 - Prob. 14.34ECh. 14 - Prob. 14.35ECh. 14 - Not all aldehyde give a positve Bendicts test....Ch. 14 - A stockroom assistant prepares three bottles, each...Ch. 14 - Glucose, the sugar present within the blood, gives...Ch. 14 - Fructose, present with glucose in honey, reacts...Ch. 14 - Prob. 14.40ECh. 14 - Prob. 14.41ECh. 14 - Complete the following equations. If no reaction...Ch. 14 - Complete the following equations. If no reaction...Ch. 14 - Describe the products that result when hydrogen...Ch. 14 - Prob. 14.45ECh. 14 - Draw structural formulas for the products of the...Ch. 14 - The following compounds are cyclic acetals or...Ch. 14 - The following compounds are cyclic acetals or...Ch. 14 - Write equations to show how the following...Ch. 14 - Prob. 14.50ECh. 14 - Identify the most important aldehyde and ketone...Ch. 14 - Using Table 14.3, name an aldehyde or ketone used...Ch. 14 - Prob. 14.53ECh. 14 - CH3COH(O)CH3COOHacetaldehydeaceticacid You need to...Ch. 14 - The addition of water to aldehydes and ketones...Ch. 14 - Prob. 14.56ECh. 14 - Formaldehyde levels above 0.10mg/1000L of ambient...Ch. 14 - In the IUPAC name for the following ketone, it is...Ch. 14 - Why can formaldehyde (CH2O) be prepared in the...Ch. 14 - Other addition reactions of aldehydes occur....Ch. 14 - Prob. 14.61ECh. 14 - Prob. 14.62ECh. 14 - Vanilla flavoring is either extracted from a...Ch. 14 - Prob. 14.64ECh. 14 - The use of acetone in laboratory experiments must...Ch. 14 - Prob. 14.66ECh. 14 - Prob. 14.67ECh. 14 - Which of the following would be classified as a...
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